What Claude (Anthropic) with web search answered for tax preparation software (freelancers) on 2026-09-29
Claude (Anthropic) with web search claude-opus-5 asked 2026-09-29
On 2026-09-29, Claude (Anthropic) with web search was asked "best tax preparation software for freelancers". It named 11 brands; the first six, in order, were FreeTaxUSA, TurboTax, TurboTax Premium, QuickBooks, H&R Block and H&R Block Self-Employed.
| Question | best tax preparation software for freelancers |
|---|---|
| Asked on | 2026-09-29 |
| Engine | Claude (Anthropic) with web search |
| Model | claude-opus-5 |
| Brands named | 11 |
| Sources cited | 6 |
| Audience | freelancers |
| Coverage | Coverage: Claude (Anthropic) with web search. Other engines not included. |
| Last verified |
Coverage: Claude (Anthropic) with web search. Other engines not included.
The question asked, verbatim: best tax preparation software for freelancers
Brands named, in the order the engine gave
- FreeTaxUSA recommended
FreeTaxUSA - My default pick for most freelancers.
- TurboTax recommended
The interface is plainer than TurboTax's, but if you already know roughly what your deductions are, you're paying ~$15 instead of ~$190 for an identical return.
- TurboTax Premium recommended
TurboTax Premium (the old "Self-Employed" tier) - Worth the money in two specific cases: it's your first year with 1099 income and you want heavy hand-holding through Schedule C, or you already use QuickBooks and want your categorized expenses to import directly.
- QuickBooks recommended
TurboTax Premium (the old "Self-Employed" tier) - Worth the money in two specific cases: it's your first year with 1099 income and you want heavy hand-holding through Schedule C, or you already use QuickBooks and want your categorized expenses to import directly.
- H&R Block recommended
H&R Block Self-Employed - The sensible middle.
- H&R Block Self-Employed recommended
H&R Block Self-Employed - The sensible middle.
- TaxSlayer Self-Employed recommended
TaxSlayer Self-Employed - The cheapest paid option with real support.
- Cash App Taxes recommended
Cash App Taxes - Free federal and free state, and it does support Schedule C.
- Keeper mentioned
- Keeper or Hurdlr for year-round expense and mileage capture.
- Hurdlr mentioned
- Keeper or Hurdlr for year-round expense and mileage capture.
- S-corp mentioned
- A real CPA or EA once you clear roughly $75-100K in net profit, or the year you consider an S-corp election.
What Claude (Anthropic) with web search answered about tax preparation software for freelancers on 2026-09-29: 11 brands named, 6 sources cited. This question is asked again on the nightly schedule and each new answer gets its own dated page.
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Sources the engine cited
| Source | Type |
|---|---|
| cnbc.com | other |
| freetaxusa.com | vendor |
| hrblock.com | other |
| smartasset.com | other |
| thecollegeinvestor.com | other |
| primewayfcu.com | other |
The answer, as recorded
Here's what I'd actually recommend, roughly in the order I'd suggest trying them: **1. FreeTaxUSA** - My default pick for most freelancers. Schedule C, home office, SE tax, depreciation, and Schedule D are all included in the free federal tier; you only pay ~$15 per state return. It's an IRS-authorized e-file provider and the math is the same math everyone else does. The interface is plainer than TurboTax's, but if you already know roughly what your deductions are, you're paying ~$15 instead of ~$190 for an identical return. **2. TurboTax Premium (the old "Self-Employed" tier)** - Worth the money in two specific cases: it's your first year with 1099 income and you want heavy hand-holding through Schedule C, or you already use QuickBooks and want your categorized expenses to import directly. That integration genuinely saves an evening of work. Otherwise you're paying roughly $130 federal + $65 state for convenience. **3. H&R Block Self-Employed** - The sensible middle. Nearly all of TurboTax's guided experience at meaningfully less (~$115 + $45 state), and it's the only one of these where you can hand a messy year to a human in a physical office if you get stuck. **4. TaxSlayer Self-Employed** - The cheapest *paid* option with real support. Flat pricing, includes self-employed guidance and tax-pro access. Good if FreeTaxUSA feels too bare but you won't pay TurboTax prices. **5. Cash App Taxes** - Free federal *and* free state, and it does support Schedule C. The catch: no multi-state returns, no filing for part-year residents in some situations, and support is thin. Great if your situation is simple; check the unsupported-forms list first. Two things that aren't filing software but matter more than which of the above you pick: - **Keeper** or **Hurdlr** for year-round expense and mileage capture. Most freelancers overpay because they can't reconstruct deductions in April, not because their software was wrong. Hurdlr is the better of the two for real-time quarterly estimates. - **A real CPA or EA** once you clear roughly $75-100K in net profit, or the year you consider an S-corp election. At that point the tax planning is worth more than the software fee difference. One caveat: tax software pricing changes every season and the tiers get renamed, so confirm the current price on the provider's own site before you commit - the figures above are from this season's comparisons. Sources: - [CNBC Select - Best tax software for small businesses](https://www.cnbc.com/select/best-tax-software-for-small-businesses/) - [FreeTaxUSA - Free federal filing / supported forms](https://www.freetaxusa.com/software/) - [H&R Block - Self-Employed Online](https://www.hrblock.com/online-tax-filing/self-employed-online-tax-filing/) - [SmartAsset - H&R Block vs. TurboTax (2026)](https://smartasset.com/taxes/hr-block-vs-turbotax) - [The College Investor - TurboTax vs. H&R Block vs. TaxAct vs. TaxSlayer pricing](https://thecollegeinvestor.com/15201/comparing-prices-turbotax-hr-block-tax-act/) - [PrimeWay FCU - TurboTax vs. H&R Block vs. TaxAct vs. TaxSlayer vs. FreeTaxUSA vs. Cash App Taxes](https://www.primewayfcu.com/blog/turbotax-vs-hr-block-vs-taxact-vs-taxslayer-vs-freetaxusa-vs-cash-app-taxes)
Near this answer
The same question, recorded on other dates: 2026-09-27, 2026-09-25, 2026-09-23, 2026-09-21, 2026-09-16, 2026-09-14, 2026-09-12, 2026-09-10, 2026-09-08.
tax preparation software, asked for other audiences: small businesses (asked 2026-09-29), nonprofits (asked 2026-09-29).
Other categories with a recorded answer: accounting software, accounts payable automation, audit management software, bookkeeping services.
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Answer Watch records what one AI answer engine said on one date, nothing more. Each page names the engine and the model, carries the date the question was asked, and lists the brands that appeared in the answer in the order the engine gave them, with the sources it cited. It is a measurement, not a ranking, not a recommendation and not a claim about the world. Brands that did not appear in an answer are not named on any public page. Coverage: Claude (Anthropic) with web search. Other engines not included.